62. Sexual Adventures of Pre-DD Jenny

Mike gave me the suggestion (or is that an order?) to write about my sexual experiences in my younger daze, um, I mean days. I might as well start from the beginning, way back to my virgin days. Yes, hard to imagine, but I was once a virgin.

I joke that by the time I had sex with a guy (at age 17) I was a very experienced virgin. By the time the “magic moment” arrived I was well versed in mutual manual and oral stimulation – both with guys and yes, with girls (actually, girl, as in singular). My first sexual experience was in 1984, before it was an in-thing to be bisexual / lesbian. Not to say it is always accepted today, but it was not talked about back then and definitely not something you wanted people to know about.

I’ve know my best friend for life, Amy, since kindergarten. She lived just a few blocks away and we were extremely close. So fast forward to when we were 15. We had seen each other naked countless times so it wasn’t even a thing. Amy had a swimming pool in her backyard and it was pretty secluded, so one of us, not sure which, got the idea to skinny dip. We would get freaked out every time we heard a noise that sounded like a car pulling up or a car door closing. We would run and grab our suits and then laugh when no one was there, then get naked again.

One day we were finished with a swim and we were in her bathroom drying our hair. We both had shorts on but no tops. I commented about her breasts, which I’ve done before, regarding her abundance and my lack thereof (she developed quite early and rapidly). She made some comment about me being obsessed with her tits because I always stared at them and talked about them. Guilty as charged! I said something about them looking so squeezable or something like that and she said something like, “Well, give them a squeeze and see.” It wasn’t a sexual thing, it was just playful and innocent, or at least seemed that way. Well, apparently I groped her for several minutes in a trance like state. We were real quiet while I squeezed and gave her a major feel up. Her nipples got big and when she noticed it she broke the trance by covering her tits with her arms and moving my hand away and saying “enough!” We then both just laughed and I said something like, “Yep, they are squeezable.” That was that. Nothing more to it.

It wasn’t much longer after that day that Amy and I were talking about masturbation. That was a common topic for us as we would tell each other about our favorite things to hump and pretend. She told me that ever since I “felt her up” (as she referred to it), she realized how good it felt to play her nipples. I was quasi-offended at her statement that I “felt her up” and part-joking/part-serious said that “I did not feel you up! I was just curious!” Amy then said something like, “Well, I am curious too. Can I feel yours?” So, I let her. It wasn’t long before we both had our hands in each other’s shirt. This curiosity turned sexual.

Without going into all the details, the curiosity that we satisfied that day with a mutual grope session turned into greater curiosity and greater satisfaction on subsequent days and weeks. While we took it slow, it eventually led to us exploring many facets of lesbian sex. Neither of us felt bad about it. We both liked boys (a lot) and both felt like we weren’t “having sex with another girl.” We were just having sex with each other. It was nice that we never attached anything negative to what we did. I think that healthy beginning, added to my zero sense of shame, set the stage for a positive outlook on all things sex and my sexuality.

I’ve got a lot of Amy sex stories, not all involving just her and I messing around. We also roomed together in college. I could fill several posts with our many adventures. Perhaps another time, and I’ll stick to the stories that occurred at age 18+. It’s kinda’ creepy thinking about who might be getting aroused by stories of my early pubescent romps (yes, I am talking to you, you sick f*ck!). Just kidding.

A word from Mike: Hello all, not sure what to add, but Jen asked that I occasionally share my reaction to a post. Not much for me to react to as these stories are old news to me. Jen had confided in me about her and Amy back when we were in high school, and the story of their initial fun together is tame compared to other stories. We have nicknames for some of those stories such as “Strip Quarters,” “Night Swimming,” “Pube Shaving Party,” and “Reunion.” I’ll let Jen reveal those in time. I’ve never known Jen to be shy in the bedroom, but even after all these years and 25 years of marriage, the last year and half have definitely taken things to an entirely new level of exploring. I am a lucky guy.